Potassium Carbonate → HCID 87242428, compound

HRID 2048145Notes

Reaction equation

HRID 2048145 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:5]2=[N:4][C:3]=1[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+].O.C(O)C>C1(C)C=CC=CC=1.O>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[N:6]3[CH:7]=[CH:8][CH:9]=[N:10][C:5]3=[N:4][C:3]=2[C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 19096565Water ethanolHCID 86631781HCID 86631781, compound

Product 1

HCID 87242428HCID 87242428, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

0.225 g (0.74 mM) 4-(3-bromoimidazo[1,2-a]pyrimidin-2-yl)benzaldehyde is dissolved in 5 mL of toluene. To this mixture is added 4-fluorphenyl boronic acid (1.5 eq) followed by tetrakis triphenylphosphine palladium (0) 10% by wt, K2CO3 (3 eq) and ethanol water mixture (4 mL). The reaction mixture is heated at 90° C. for 4-6 h. The reaction is cooled to room temperature and 20 mL of water is added and the reaction mixture is extracted with ethyl acetate. The organic layer is dried and concentrated. The crude is purified by flash column chromatography to yield the desired compound.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. extractionthe reaction mixture is extracted with ethyl acetate
  3. customThe organic layer is dried
  4. concentrationconcentrated
  5. customThe crude is purified by flash column chromatography

Sources & evidence

ORD record
ord-01286cd7c7534eb89227b72c120a1a94
Source dataset
uspto-grants-2013_11
Patent number
US08592591B2

Reaction notes

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